


37 years and 23 guys

by AquaCitty



Category: Supernatural
Genre: (That's not really explored as much as his bisexuality), Angst, Bi Dean, Bisexual Character, Demiromantic Dean Winchester, Fluff, Honestly pls read bc I worked SO hard on it, I'm lowkey proud of it too, M/M, SO GAY, Smut, Though there is smut it's not just porn, mostly story istg
Language: English
Status: Completed
Published: 2020-09-29
Updated: 2020-10-06
Packaged: 2021-03-08 03:33:57
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 8
Words: 5,181
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26719090
Author URL: https://archiveofourown.org/users/AquaCitty/pseuds/AquaCitty
Summary: It took Dean Winchester 37 years and 23 guys to comes to terms with who he is.(AKA Dean's journey to discovering his bisexuality and being okay with it.)
Relationships: Castiel/Dean Winchester, Dean/Multiple Male Characters, Dean/Multiple Male OCs
Comments: 9
Kudos: 50





	1. Owen

**Author's Note:**

> You might want to read this on the 'Entire Work' mode as I wrote it all together, not in chapters. But it's up to you!
> 
> TW (for whole work):  
> Swearing  
> Explicit sex  
> Use of slurs (Only once rn)  
> Homophobia (Mainly internalized)

The first guy he ever did anything with was Owen Trevor. He was 18, drunk off life and tequila. Owen was tall with dark skin and darker hair, and blatantly flirting with him. So Dean did the unthinkable, he kissed him, smashed his lips against Owen’s. It felt good, it felt right, Dean ignored the way his heart beat hard enough to break his ribs and just smirked up at him.

“Let’s get out of here.” Dean said with much more confidence he felt, and Owen grinned, nodding. 

Owen’s place was closer, so they ended up there, hungrily kissing each other as they knocked into walls and furniture as they found their way to the bedroom. Dean secretly loved it when Owen took control, pinning him against the bed, sucking a deep mark into his neck. 

Dean whined, balling up the bedsheets in his hands. 

It was messy, quick, and red hot. Owen ended up sucking Dean off, while Dean finished him off with a handjob. 

And they fell asleep in each other's arms. 

Dean got up at 2 am, his head pounded, and his body filled with regret and disgust looking at Owen’s sleeping form. 

_ I was drunk, it doesn’t count _ , he told himself. 

And he really believed it too, forcing himself to forget the euphoria of the night. 

He slept with 3 more women that week, as if trying to wash himself clean. 


	2. Isaac (& Greg, & Jamie)

Over the next 8 years he slept with three more men. Him and Greg had a devil's threeway. That doesn’t count, he insisted. And Jamie happened after Sammy had just left and he tried coke for the first time, so definitely doesn’t count. But Isaac… Isaac was different… 

The night didn’t start off differently, he had just ganked a pack of werewolves with his dad, who had taken off without so much as a goodbye. So he went to a bar, ready to drown out his sorrows. Isaac was the bartender. He had long brown hair pulled back in a bun, and gorgeous hazel eyes, and, well, Dean always had a thing for bartenders. 

On his 5th shot, he winked messily at the guy, who just giggled. Dean’s heart clenched at the sound,  _ cute _ , he thought absentmindedly. 

“When do you get off beautiful?” Dean asked, his speech slightly slurred. 

Isaac leaned against the bar, smiling genuinely “Around half an hour gorgeous.”

Dean swallowed, looking him up and down without realizing it, “Meet me outside?” 

“I can do you one better, I live right upstairs, just wait for a bit and I’ll take you up there.” Isaac told him. 

Dean grinned goofily. “I’ll see you there… uh…” he trailed off. 

“Isaac, Isaac Holland.” 

“Dean, Dean Winchester.” Dean extended his hand, and Isaac shook it with a bashful smile. 

Half an hour later, Isaac looked down at him with the same look, before straddling Dean on his bed and kissing him gentle and slow. 

It was new for Dean, with guys it had always been rushed, hard, hungry. But not with Isaac. 

Somehow they ended up naked, still kissing slowly, as Isaac jacked him off lazily. 

“Turn around,” Isaac whispered sensually. 

Dean tensed, and Isaac suddenly backtracked. 

“Unless you don’t- I’m usually a, uh, top but-” Isaac stuttered. 

Dean cleared his throat awkwardly, “Yeah, no, I- I’ve just never done  _ that _ .”

“Bottomed?” Isaac asked. 

Dean’s face flamed in embarrassment, “Uh, yeah, that.” 

“Wanna try?” Isaac whispered into his ear before kissing it. 

Dean’s dick twitched in interest, and who was he to deny Dean Jr.?

“Yeah… okay.” He breathed. 

Dean turned around, Isaac kissed down his back gently, and Dean shivered. 

He grabbed the lube, slathering it on his fingers. Then he crawled behind Dean, teasing his hole with a single digit. 

Dean hissed as Isaac slowly worked in one finger, he then moaned as he grabbed his cock and resumed his earlier handjob. The stimuli together was weirdly… pleasant.

After a few moments he slipped in another finger, and curled them until he hit- holy  _ fuck _ . 

Dean moaned loudly as Isaac hit his prostate. 

“Goddamn.” He groaned, and Isaac giggled again, which was slowly becoming Dean’s favorite sound. 

The rest of the night felt like a blur after that, Isaac fucking into him became better and better with every movement, and suddenly Dean came. Hard. Isaac pulled off, finishing himself off with his hand, coming accidentally on Dean’s back. He apologized for it, but Dean waved him off, he was weirdly fine with it. 

Isaac kissed him, telling him to stay as he got a wet rag, and cleaned up Dean gently as he could as he fell into a deep sleep. 

In the morning Dean’s head still killed, reminding him that last night was just a mistake, a drunken mistake because it had to be. 

Still it was hard to feel regret when Isaac gave him his number as he was leaving, giggling at some dumb joke Dean had made… but he was drunk… so it didn’t count… right? 

He pushed that doubt down the deepest depths of his mind, even further when he reconnected with Sammy to look for their Dad. 

Until one night. 

**Notes for the Chapter:**

> I lowkey made myself sad writing this bc I started to ship Dean and Isaac whoops


	3. Caleb

**Notes for the Chapter:**

> Set in S1 E16

They were working a case, interviewing locals, when a cute bartender, Caleb, pushed his number towards Dean, his smile reminded him of the bartender he hooked up with almost three years ago now. 

Dean smiled awkwardly, but took the number anyway… Dean watched as Caleb walked away, and let his jaw unclench. No one saw, and he was pretty hot, okay really hot. 

Dean moved on, chatting up a waitress for more information. She didn’t have anything to add, so he went back to Sammy. 

“Talked to the bartender.” He announced. 

“You get anything? Besides her number?” 

Her? Oh. He almost corrected him, but thought better of it. If Sam didn’t see Dean and Caleb talking, well that was for the better anyway. 

“Dude, I’m a professional, I’m offended that you would think that…” Dean said defensively. 

Sam looked unconvinced. 

“Alright,” Dean sighed, bringing out the number with a grin. Hey a number is a number! Sober Dean might not agree, but his alcohol addled brain was happy about it. 

“You mind doing a little bit of thinking with your upstairs brain, Dean?” Sam said, pursing his lips. 

“Huh?” Dean asked dumbly. 

Sam raised his brows skeptically. 

“There’s nothing to find out!” Dean argued, and it was true, no one had seen anything unusual. 

As Sam was explaining his research, he looked down at the number with a grin, and as Sam finished his explanation saying he’s found nada, Dean told him, “So, to recap, the only successful intel we’ve scored is the bartender’s phone number.” 

Sam looked at him with his typical “I can’t believe I have to deal with this shit” expression, which Dean took as a win. 

As Sam followed up on a lead, Dean went back to the bar. He was still buzzed so when he found Caleb in a dark alley by the bar and when Caleb kissed him, Dean somehow ended up on his knees. His heart hammered, expecting someone to walk in on them every second, but in a way it made it feel more exciting. That was until Caleb came unexpectedly down his throat. Dean started to swallow until his eyes widened and the bubble of happiness around him popped. 

_ I just swallowed cum, _ he thought dumbly _ , I’m such a fucking faggot. _ He stumbled back, spitting out the rest of the liquid in his mouth and practically sprinted to Baby, desperately trying to ignore the way his dick strained against his jeans. 

After taking a cold shower he dove headfirst into the lore, not taking a break until he figured out this symbol he and Sam had discovered earlier. After many books and websites Dean found it, it was Zoroastrain symbol. He called up Sam and told him the good news. 

“How’d you figure that out?” Sam questioned, sounding impressed. 

“Give me some credit, man. You don’t have a corner on paperchase around here.” 

“Oh yeah? Name the last book you read?” Sam scoffed. 

Dean frowned, he didn’t feel like arguing right now. He quickly said the first excuse that came to mind. 

“I called Dad’s friend Caleb, he told me alright.”

Well, shit. He tried to ignore the way his stomach lurched at the name, from guilt? Disgust? He wasn’t sure. 

“Yeah.” Sam chuckled. 

Dean shook his head, skillfully burying his feelings deep down, and continued to explain about the symbol and what it entailed. Sam hung up on him when he pushed him to hook up with this Meg chick. Pussy. 

He decided to keep grinding, he pulled out his phone from his pocket and dialed Amy, a chick he was flirting with from the police department, looking for more intel on the two victims. 

A few hours later, everything had gone to shit, him and Sam were tied up, and Meg was using them as bait for their dad. 

Thinking about Dad made Dean’s mouth go dry. He felt dirty, like Dad would sense what he’d done with Caleb that same day. Fuck. How could he be this stupid. 

They got out and made a run for it and there he was. Just in their hotel room like no big deal. Of course it all disappeared when he finally saw him. His father stood by the window, and nothing else matters. Dean strutted over to him and pulled him into a hug, he refused to let tears fall. And when he was forced to leave he refused to acknowledge the small part of him that felt relieved to see him go. 

Then, months later, he died. And it was devastating, everything was confusing, and unknown, but somehow… it was also more free. And that was terrifying. 

He thought if he told enough people he “didn’t swing that way” maybe it’d come true. It didn’t work. He just liked sex, he argued with himself, he’s still straight. He just can’t tell the difference when he’s drunk. Definitely still straight. 

And then he saw Ash. 


	4. Ash

**Notes for the Chapter:**

> Set in S2 (Obviously)

It wasn’t love at first sight or anything, in fact Dean was pretty underwhelmed by Ash at first. But then he started to flirt, looking up at Dean with a determined stare. Dean’s face felt hot, and he glanced at Sammy, but he was off talking to Ellen behind the bar. Oh what the hell? Who was Dean to back down from a challenge? So he flirted back, and for a while that’s all it was. Flirting more brazenly every time they saw each other, But then one day he asked for Ash and was told he was in his room. 

Dean walked to the back, and knocked on the door, “Ash? Dude, you in there?” 

Jo walked by and smirked at Dean, “He’ll only answer to Dr. Badass.” She informs him, pointing at the sign declaring ‘Dr. Badass is in’ on Ash’s door. 

Dean sighs, and raps on the door again, “Dr. Badass?” 

Jo giggles, and leaves Dean alone, after a second Ash opens the door, peeking his head through. “Yo.” 

“Hey,” Dean greets him, “Can I come in?” 

Ash nods, and opens the door, revealing himself to only be wearing boxers. 

Dean’s eyes widen in surprise, and his gaze lingers on Ash’s crotch for a second too long. 

“Like what you see?” Ash teases, stepping aside to let Dean in. 

“Maybe.” Dean smirks, sounding a lot braver than he felt. 

Ash looked up at him, and Dean swallowed harshly. He knew that look, he’s seen it way too many times, it’s the ‘we’re _so_ going fuck soon’ look. 

“Want some weed?” Ash asks. 

_Thank fuck. I can’t do this shit sober._ Dean thinks, he doesn't say that of course, instead he just nods.

So they get high, and they joke, and flirt, and tease, and suddenly they’re kissing and then their clothes are coming off, and pretty soon, Dean is clutching Ash’s hips for dear life as he ruts into him. 

Dean bites his lip as Ash comes with a cry, and he lets himself go a few moments later. 

He pulls the condom off, throwing it into Ash’s bin, and collapses onto the bed. 

“Holy _shit_ , you’re good at that.” He tells Ash truthfully. 

Ash chuckles, he’s already lit another blunt, “You’re not too bad yourself mi amigo.” 

Ash passes the joint, and Dean takes a hit without thinking much of it. And for the first time ever Dean stays after hooking up with a dude. 

With Ash it feels easy, it’s simple, fun, good. 

He comes back a lot, especially when he’s in a dry spell, and Ash is always up for it. 

He’ll never admit this, but it was probably his longest running relationship since… well, actually, ever. 

He even got him a gift, didn't think much of it, though. A victim gave him and Sam some stuff for getting rid of her late husband’s ghost, including a large gold watch he almost threw out. Sam stopped him ("You can't just throw it out, it disrespectful!"), so he pocketed it. 

The next day Ash had pulled off Dean's jacket, when it hit the floor there was a loud bang. Dean sat up with a jolt. 

“Oh shit.” 

“What?” Ash asked, concerned. 

Dean hopped out of bed, retrieving the watch. “It was a gift, Sam won’t let me throw it out.” He explained. 

“Why’d you want to?” Ash asked, taking the watch off Dean. 

Dean raised his eyebrows if if to say 'really?'

“You can have it if you want.” He told Ash absentmindedly. 

“Seriously?” 

“Yeah go for it.” 

“Ohmygosh _babe_ . You got me a _present_?” Ash teased, putting on a valley girl accent. 

“Fuck off.” Dean grinned. 

It was the watch he was wearing the day he died. 

And that fucking killed Dean. He was dead, he was gone, and he was never coming back. Dean wasn’t in love with him, but that doesn’t mean he didn’t love him. It was unfair, it was all so unfair, everyone he'd ever cared about was being picked off one by one by the yellow-eyed demon. He clenched his jaw. He was going to kill that son of a bitch. 

And he did. But not before he took the thing that meant the most to Dean in the world. Sam. 

And that was the final straw, he wasn’t going to let Sam die. So he decides he deserves to be a little selfish, and he brings Sam back in exchange for his soul and his life in one year. 


	5. Alex, Nick, & Digger

**Notes for the Chapter:**

> Alex Doublemint = S3 E1, Nick Monroe = S4 E14, & Digger Wells = S5 E15

He would do it over again in a second if he had to, but that doesn’t mean he isn’t scared as hell for… well… hell. 

So he decides to make his year worth while with booze and girls… and maybe guys. 

_So maybe I’m bicurious or whatever those damn websites say._ He decides. 

So he hooks up with the Doublemint twins, Alex and Tanya, he even asks Sammy for a lift. That turned out to be a shitty idea as Sam walked in on Dean with his dick in a man’s ass, and they spent the ride back in stark silence. 

“You know they don’t count, two guys and a girl, it- it doesn’t count.” He tells Sam when they neared their hotel, but sounds like he’s trying to convince himself. 

Sam looked at him with an indecipherable expression, “I never want to see that much of you ever again.”

Dean nodded, “Fair.”

He didn’t get the chance to hook up with any more guys that year, and for the first time ever he allowed himself to acknowledge he was kind of upset about it. 

But he didn’t get much time to ponder that because suddenly he was dragged to hell and for forty long, long, years his life was only pain. 

And then he was out and everything still fucking sucked, because he just felt so, so empty inside. He couldn’t forget a single detail. A single screaming face of the souls he tortured. Sex was the last thing on his mind. 

Even when he met the dark haired, blue eyed angel that raised him from perdition. 

Then days went by, then weeks, then months. He starts to smile again, and he thinks maybe if he stops the apocalypse that maybe, just maybe, the guilt would be a little easier to deal with. 

Then Sam gets addicted to demon blood and he doesn’t know what to do. So when a cute FBI agent likes rock n’ roll, and old cars, and him, he decides fuck it. That’s how he ends up under the spell of Nick Monroe, who ends up being a siren… Great taste in men, as you can see. 

Dean can’t stand the way Sam looks at him after he comes out of the spell, so he tells him Nick slipped something in his drink, and doesn’t look back to see if Sam believed him. 

It was almost a year before he hooked up with another guy. Digger Wells, town drunk, according to Bobby. 

He gave Dean a look that seared into his soul, an unspoken challenge, fuck with me and see what happens. Dean took on the challenge gracefully, making Wells call out for the God Dean knew wasn’t in heaven. 

He was sober too, completely, or as completely as Dean could be, but still he hid it and buried it. And when Bobby questioned the hickey on his neck he dove into a raunchy story about a waitress that made Bobby laugh and Sam cringe. 


	6. Cas

**Notes for the Chapter:**

> Set mid-season 6, after Dean breaks up with Lisa.

It was Cas who forced him to confront it, because of course it was. 

It’s not like he hadn’t noticed Cas was just his type. Strong, tall, broad, dark hair, with light eyes. And it’s not like he hadn’t noticed the way his eyes are always drawn to Cas’s lips. Or how the air seems alight with electricity when they stand too close.

Cas hasn’t been himself lately, the war in heaven was apparently taking its toll, so Dean was starting to expect the unexpected from Cas. 

But nothing could have prepared him for the angel appearing in his room, and simply asking Dean. “Will you have sex with me?” 

Dean just gaped at him. 

“You enjoy meaningless flings, and we are comfortable with each other, you seemed an obvious choice.” 

“Cas, don’t you think a girl would be a better choice?”

“Gender isn’t a matter of importance in terms of angelic attraction.”

Dean paused, “O-kay, but it is for humans.” 

Cas squints in confusion, “I understand, but you take both female and male lovers, do you not.” 

Dean’s breath shallowed, “What the fuck. H-how do you-?” 

“I raised you from hell, Dean, I saw your life’s story when I touched your soul.”

Dean swallowed harshly, “A-And you’re okay with that?” 

“Of course Dean, your bisexuality makes no difference to me at all.” 

“Bisexuality?” Dean whispered to himself, somehow the label felt right, but also wrong.

“So, will you have sex with me?” Cas repeated the question after a moment. 

“Why do you want to do... that... with me?” 

Cas looked down, abashedly, “I heard sex helps one forget their problems.” 

Dean’s heart ached, “Oh.” Is all he said. 

“Will you?” Cas asked a third time, looking up, and Dean recognized the desperation in his eyes, the longing to get away for just a moment and so he nodded. 

Cas took two long strides forward before cupping Dean’s face and pulling him into a kiss. It started slow until it wasn’t anymore. Dean threw Cas down on the bed, kissing down his chest, determined to make Cas forget about his pain, forget about whatever is bothering him. 

It was so worth it, making a literal angel moan, and swear, might be one of Dean’s greatest accomplishments. 

For the first time Dean didn't worry about himself during sex, wanting to worship every inch of Cas’ body. That is until Cas pushed Dean's mouth off his dick, turning Dean around with superhuman strength. And he moaned as Cas prepares to top him for the first time in more than a decade. 

“You look beautiful like this.” Cas whispered into his ear, and Dean’s heart fluttered. 

Cas pulled his fingers out, and lined himself up with Dean, hitting Dean’s prostate with every thrust. Dean later discovers it’s an unintentional part of the angelic lineup, so he can literally thank God for it. 

Dean came unraveled under Cas, hissing due to overstimulation as Cas continued to thrust a few times before coming inside him. 

Then, with a click of Cas’ fingers, they were cleaned up. 

Dean chuckled, “That’s useful.” He yawned. 

“That was helpful…” Cas determined in his gravelly voice, “Thank you.” 

Dean looked at him sympathetically, “Cas you know if you need help-”

“I know.” Cas cut him off. “I have to go.”

Dean sat up, almost asking him to stay, but as quickly as he was there he was gone. 

Dean sighed, laying back and going to sleep.


	7. Benny, & Cas

**Notes for the Chapter:**

> Mainly set between S7 & 8, and during S8 (Obviously)

Dean is the last person to believe in fate, but sometimes he truly believes after that night it was sealed. Even after all the shit Cas pulled he still felt a connection to him, deeper than anything he’s ever felt. It was new and scary, and when Cas died, he was devastated. 

Then Cas came back, and he saved Sam, and then he was gone again. Well, in all the ways that counted, because even when Cas was there… he wasn’t _Cas_. 

Dean thought about that night a lot over the next few years, he tried to forget the way his heart soared when Cas kissed him, when Cas accepted him. Before Cas fucked everything up. 

Bisexuality, the word left a bad taste in his mouth. He looked it up, scouring definitions online more often than he’d like to admit, and it fit him… it really did. So why did it feel so wrong?

Then suddenly none of that shit mattered, because who can worry about labels in Purgatory? It was life and death. Love, sex, friends, enimies, who the fuck cares? 

Benny didn’t. 

When Dean woke up from a nightmare, and kissed him, half out of his mind, Benny didn’t care. He kissed him back, hard, and fucked him harder. 

Cas did care though, somehow he kept his loyalty, his love, in that nightmare of a world. He was always so ready to sacrifice himself for Dean. And Dean couldn’t help loving him, needing him, wanting him. Love, lust, co-dependence? Who knows what it was, but it didn’t matter. 

So when Benny kissed him hungrily after a few weeks of travelling with Cas, ready to take the edge off, like they always did, Dean pulled away guiltily. 

Benny glanced between Cas and Dean, Dean’s gaze was glued to the ground, while Cas was staring daggers. 

Benny held his hands up in surrender, “Sorry brothers, didn’t realize you two were-”

“We’re not anything.” Cas growled, “Please, go ahead, I’ll keep watch.” 

He stalked off and Dean sighed jogging after him. 

“Cas. What’s wrong?” 

Cas scoffed, “Nothing. I just- I should've known, even in here you’d find a meaningless person to fuck.” 

The swear sounded strange coming from Cas’ lips. 

“Benny isn’t meaningless, he’s… helping us.” Dean said, before a sudden wave of anger rolled over him. “And Cas you don’t get to fucking judge me, I’m just trying to survive this place.” 

“You need sex to live?” Cas questioned angrily. 

“No! But I need _something_ to remind me I’m _human_.”

“Then use me.” Cas growled. 

He flew right in front of Dean, pulling him into a searing kiss before he could pull away. Dean melted into him. 

“ _I’ll_ remind you you’re human.” Cas whispered, dropping to his knees. 

Dean frowned at Cas’ possessive tone, but he didn’t object when he pulled down Dean’s jeans and boxers.

It didn’t take long for Dean to finish, his head rolled back, and his breath coming out in short bursts. 

“I was starting to think you two died.” Benny’s voice cut through the forest. 

Cas stood wiping the corner of his mouth. 

Benny looked him up and down with a calculated gaze. 

“Need some help with that?” He looked pointedly at Cas’ crotch. 

Cas squinted him as if considering his offer, “No thank you.” 

“Suit yourself.” Benny shrugged, “We should set up camp for the night, we all need rest. I’ll take first watch.”

And that was how it went for a while, Cas and Dean fooled around, while Benny waited patiently, offering to join in, always directed to Cas. But Cas always said no, that was until one day he said yes. 

Even Cas looked a bit surprised at his answer, but it was hard not to trust each other after fighting side by side day after day after day. 

So that’s how it went, every time they needed an escape, they’d just kiss the person closest. It was how Dean kept his sanity. 

And then sometimes they’d talk, all three of them, about the smallest things to the largest. Benny taught them the tricks he’d learnt in Purgatory, while Cas shared wisdom he learnt in Heaven. Sometimes it was even… nice. At least life was simple. Eat, kill, fuck, talk, kill, sleep, and repeat. 

Dean wasn’t sure if time really went slower there, but it felt like a decade had passed by the time they reached the portal. 

And then Cas didn’t make it out. 

Dean tried, he really, really tried, but Cas didn’t make it out. 

He was spit out on earth, and every instinct in him screamed at him to go back, to save Cas, to save his angel. But he couldn’t. 

It hurt Benny too, he could see it in his eyes. And that was almost worse... without Cas, being with Benny felt… incomplete. So when Sam gave him an ultimatum, Benny or him, Dean told himself it was the right thing to say goodbye, but he really knew, in his heart of hearts, he was doing it to protect himself.

Then Cas came back and Dean couldn’t believe his luck. For a while Sam was always there, hovering just in the background, but then he left for a food run, and Dean and Cas were alone… 

They locked eyes, and Dean held his breath, they were each waiting for each other to make a move. 

“It’s good to see you back, buddy.” 

“It is good to be back.” 

Awkward silence stretched out, filling the room with a tension that seemed almost tangible. 

Eventually Cas squinted his eyes at Dean, in a silent question, which Dean interpreted as _‘Are we still… whatever we were back there?’_.

Panic bloomed in Dean’s chest. In purgatory, sex was sex, and love was love, and there was no one there to judge him, but now they’re back on earth, and Cas’s hopeful gaze suffocated him. 

Dean looked away guilty, giving Cas his answer. 

_No._


	8. Aaron

**Notes for the Chapter:**

> Set mainly in S8 E13

It was the regret that made him see straight. Or, well, _not_ straight. 

It was midnight, they were in some shabby motel, cheap enough Dean decided to splurge and get separate rooms. He waltzed to the bathroom and something clicked. 

It took him off guard, but he looked at the mirror with determination. 

His senses were on high alert, as if waiting for someone else to appear, but the only noise he could hear was the insistent buzz of the fluorescent bathroom light, and the only thing he could see was his green eyes staring back at him. 

“I… am bisexual.” Dean whispered to himself. 

It felt stupid, saying it out loud, but he kept his eyes up, fighting the urge to divert his gaze shamefully. 

After a second he smirked at his reflection. He’d won.

 _Still,_ he figured _, even if I_ am _bi, I don’t have to fool around with guys._

I’m done with them. That’s what Dean decided. No more crushes, no more kisses, or hookups, or anything else. Guys are off the menu. 

He knew it wouldn’t last, not really, but he hoped it would.

Still, when a cutie a bar makes him literally fall over a table with just a smile, he sorta wants to break his pact, and when that cutie turns out to kind of be a badass, and save him and Sam’s asses, he really wants to break the pact. 

So what the hell, he does. 

He was supposed to be going to a bar, but instead he finds himself driving up a familiar driveway. 

He knocks on the door hurriedly before he can change his mind. 

A disheveled looking Aaron Bass appeared in the doorway, his tired eyes became alert upon seeing Dean. 

“W-what is it? What’s wrong?” 

Dean chuckled to himself. “Nothing, nothing. I didn’t realize my presence was synonymous with such doom and gloom.”

“What? No man it’s just-” Aaron backtracked but cut himself off, “Okay, look, when you appear at my doorstep at 2 in the morning, then, yeah, I kind of expected something to have gone down.” He finished with a laugh. 

“So what’s up?” Aaron asked after an awkward moment.

“I- uh- I just gotta know man, when you were flirting in that bar, was it real, or strictly business?” Dean answered quietly. 

“Oh my god, you’re really caught up about that, aren’t you?” Aaron snorted, “Look, it was just cause I was tailing you, but right time, right place, I would for sure flirt with you.” 

“So… you _are_ into dudes?” 

Aaron narrowed his eyes slightly, crossing his arms defensively, “Yeah.” 

“Okay good… I just wanted to make sure this was okay.” 

“If what was-” Aaron started to ask, but he was cut off by Dean’s lips crashing into his. 

Aaron quickly melted into the kiss, wrapping a hand around the back of Dean’s neck. 

When they pulled away both parties were breathless. 

“Holy shit, you’re actually gay?” Aaron spluttered. 

“Bi.” Dean said nonchalantly, as if it wasn’t the first time he’d ever admitted that to another soul. 

It was fucking amazing, saying it out loud. It felt… freeing, like a whole world of possibilities opened up to him. 

Jesus, is this what being emotionally available is like?

Aaron wasn’t his best, or his worst, honestly it felt like any other fling. Flirt with them, save them from monsters, hook up with them. 

Sure, it probably wasn’t the ideal for most people, but this is the way Dean lived. Always has been, always will be. And maybe, liking guys, doesn’t have to change that. Maybe it isn’t such a big deal after all.

Of course Dean' journey didn't end there. He had a long way to go. He made some mistakes (Crowley), and had some victories (Gunner Lawless), and of course saved the world a few more times because apparently that's his fucking job now.   
  
And, yeah, it might of taken him half a decade longer to really get his shit together, but finally (at fucking 41 years old) that blue-eyed, dark-haired Angel was his. 

**Notes for the Chapter:**

> The End!!
> 
> Also I just edited it out, bUT why did NON ONE tell me I called Aaron "Aaron Burr" and then proceded to call him "Adam" through half the chapter kjadkjdkj *Clown music plays*.


End file.
